Tin dichloride dihydrate → HCID 67113184, compound

HRID 2284311Notes

Reaction equation

HRID 2284311 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[N:4]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:3]=1.O.[Sn](Cl)Cl>C(O)C.O>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[N:4]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:3]=1

Participants

5

Reactant 2

HCID 43835034Tin dichloride dihydrateHCID 574421961-benzenesulfonyl-3-bromo-6-nitro-1H-indole

Product 1

HCID 67113184HCID 67113184, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a slurry of 3-bromo-6-nitro-1-(phenylsulfonyl)-1H-indole (2.80 g, 7.35 mmol) in ethanol (73.5 mL) was added a solution of tin (II) chloride monohydrate (6.63 g, 29.4 mmol) in water (11.0 mL) at 30° C. Once the addition was complete, the reaction was heated to reflux for 3.5 h, then quenched with 2.0 N sodium hydroxide to a pH of 8. The remaining slurry was diluted with ethyl acetate (100 mL), and the aqueous layer was removed and filtered. The organic phase was washed with 2.0 N sodium hydroxide (2×100 mL), and the combined aqueous layers were extracted with ethyl acetate (3×200 mL). The combined organic phases were concentrated to give a tacky, orange solid for 3-bromo-1-(phenylsulfonyl)-1H-indol-6-amine (2.35 g, 6.69 mmol, 91%).

Workup

  1. additionOnce the addition
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 3.5 h
  4. customquenched with 2.0 N sodium hydroxide to a pH of 8
  5. additionThe remaining slurry was diluted with ethyl acetate (100 mL)
  6. customthe aqueous layer was removed
  7. filtrationfiltered
  8. washThe organic phase was washed with 2.0 N sodium hydroxide (2×100 mL)
  9. extractionthe combined aqueous layers were extracted with ethyl acetate (3×200 mL)
  10. concentrationThe combined organic phases were concentrated

Sources & evidence

ORD record
ord-d395540db6d349289e14cfd1e24eaa77
Source dataset
uspto-grants-2015_09
Patent number
US09144557B2

Reaction notes

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